When he was 14, his father lost his job with the railroad, forcing the young boy to move in with his older sister in Jamestown, Ohio.

He shifted more deeply into the classic country sounds of artists such as Merle Haggard and George Jones.

This meeting eventually led to the Conley-Heard collaboration on the song "Smokey Mountain Memories", which made the top 10 for Street.

[2] After his discharge from the military, Conley had been playing in clubs in Nashville at night, supporting himself by working blue-collar jobs during the day.

At the same time, he was selling songs that he had written to other artists, including Conway Twitty and Mel Street, who were having much success with them.

He set a record the following year as the first artist in any genre to have four Number One singles from the same album, Don't Make It Easy for Me that was released in May 1983.

With the song, Conley also became the only country artist to appear on the syndicated music program Soul Train.

Conley recalled that he may have been the only country artist to have appeared on the Soul Train television program (he performed his duet with Pointer) and went into detail about the string of hits Randy Scruggs and he co-wrote.